I really love this place. It is what it is and it's just great. Dempseys is a quaint diner in the historic part of of Middletown, MD, on Main St. The food is good, menu pretty diverse, and prices are OUTSTANDING. There is a swivel seat diner bar in addition to the main seating area which really amplifies the character of the place. Sitting there with a coffee allows me to mentally disconnect from 2018 and takes me back to my childhood sitting in a similar scene with my dad and grandfather, and watching them talk and read the paper (they always gave me the comics section). There are a couple of specific employees who are really friendly, and overall, I recommend eating here for a quick and casual bite. There's hiking and lots of exploring opportunities nearby, and Dempseys is an excellent choice for a before or after hike meal. Enjoy! Tony read more

Unassuming on the outside but don't let that fool you. You won't leave hungry and you will definitely be back. The food and staff are fantastic; great service, great tasting fresh food and great prices. We have had just about every hot sandwich and special on the menu and we have never been disappointed. Turkey dinner night's Fridat night's are our favorites. Bring your family, go early and go hungry! Cheers to the chef for my delicious Reuben and fries last night. Hot and fresh-yummy! read more

This is a great local family restaurant. Super friendly and a town staple. Two must haves--burger deluxe or taco salad.

They have a shrimp salad in season that is a mouth experience. The beef vegetable soup is a must according to granddaughter. Also love Reuben, corn fritters & fried chicken. True homemade comfort food. Only complaint is they're only open till 2pm on Sat, Sun & closed on Monday. Might have to stop for breakfast on our way home in WA state. Come here every time we're in Maryland (twice a year). It's become a ritual with granddaughter. Tried their Maryland crab soup - so delicious! Having the crab cake burger, which I'm sure is good cuz I got the last one. It was the best crab cake I've ever had. Definitely my new fav. read more

The menu is overwhelming with choice of yummy food! Hard to select just one.... love it!

Took my son here for a quick bite for a Saturday morning breakfast. Service is down-home friendly, food is good diner food, and it is all set in a great small town. My son couldn't figure out what he wanted; when he did, it wasn't on the menu, but the waitress hooked us up and made him an al-a-carte style breakfast. My go-to breakfast spot. read more

Love this "quiet hole in the wall" restaurant. Home cooked meals that are delicious. Great place for breakfast, lunch or dinner! Closed on Monday. read more

What can I say? I got kids. You got hash browns. We were meant to be. And the homemade chili ROCKS! read more

A great diner in the heart of Middletown. The club sandwich and roast beef were great. I will definitely be back. read more

Dempseys Grille - Yummy club - Diners Near Me - Middletown, Maryland

Loved this place- a wonderful diner that filled us with delicious food after a cold night in Annapolis rocks. The crab sandwich is good and isn't too bready, chicken sandwich was great too. We'll definitely be stopping by when passing through Frederick! read more

Cute diner. Enjoyed the MD crab soup and corn fritters. Cheesesteak was really good. Iced tea was great. Service was great. Crab cake sandwich was good but I've been spoiled by Timbuktu and their massive crab cakes. We would definitely return if in the area. read more

Middletown is Lake Woebegon in central Maryland. You really can't ask much more for a hometown experience than an authentic greasy spoon like Dempsey's. The food is full-on American comfort. You'll find the place packed in the early morning and at the lunch hour on weekdays and weekends. They do breakfast really well but their cheesesteaks and homemade chili are out of this world. Let's face it though. We like the food but we really like the cozy feeling the venue and the staff engender in us. The staff is genial and friendly and the owners are usually working alongside their employees. Mike and Sybele, you're the bomb! read more

Wow! This place is a gem of a diner! We have lived in the area (Northern Va) for almost 6 months. I have yet to have decent scrambled eggs anywhere. That all changed to today. The scrambled eggs were perfect!!! Hot, fluffy and perfectly scrambled! Breakfast is my favorite meal and I will definitely be coming back! read more

We just got back from our regular Thursday night meal at Dempsey's. I ALWAYS have the spaghetti, but tonight I switched up and tried their new Buffalo Chicken salad. Outstanding! I've had them all over the country. They're a favorite. The one at Dempsey's outshined them all. A lot of buffalo chicken, plus egg, cukes, cheese, romaine, tomatoes. Perfect. I dressed it with blue cheese dressing and Dempsey's "boom-boom" sauce. Seriously, try it. I'm hoping they keep it on the menu. read more

My absolutely favorite place to be. Love the service and the food is fresh and fantastic. Home made food served hot every time. Just a great environment. read more

Thursday night's special chicken parm and Italian night. Chicken parm and homemade sauce excellent. Wife had the softshell crab and crabcake club, which was the special for the week. Outstanding! Staff is over the top friendly, and prices lowest in the county. I love how the owners are the cooks and really provide a great atmosphere. Staff is tenured which they seem to have low turn over. I hear the breakfast is terrific with low prices and no gimmicks... read more

Thanks to other reviewers we came to Dempsey's in Middletown rather than head into big town Frederick. Well worth it. Great breakfast spot with giant hot cakes, grilled and buttered biscuits and wide variety on the menu. Husband liked his biscuits and gravy. My cheese omelet was delicious. We shared a giant blueberry pancake. Yum. Servers attentive. Only downside is sidewalks are all ripped up along Main Street so be careful entering and exiting. read more

Dempseys Grille - Dempsey's grille - Diners Near Me - Middletown, Maryland

This is my favorite place for breakfast. I had the egg and cheese sandwich with white bread not toasted and instead they brought me the best egg and cheese sandwich on earth! I had chocolate milk, too and I watched how careful they were to meet my expectations. They put in the perfect amount of chocolate in it. Then, my mom got grits with butter. The total cost for all of that was 8 dollars!! (Also, they dont charge for refills:) read more

Had the 18 ounce Porterhouse steak. Very well prepared, tender and juicy. A great deal at $20. Came with a loaded baked potato which was tasty as well. Nice atmosphere. Wait staff was super friendly too. Zero complaints from this critic. read more

Service is good and it is geared to American comfort foods in my opinion. Home town restaurant and hometown feel

Small town American restaurant where the staff is like an old friend. I had the bacon, ham and cheese omelet with home fried potatoes. The ham was amazing. If I knew it was that good, I would have ordered it as a side. The omelet was excellent with a thin layer of eggs surrounding generous portions of meat and cheese. Simply Perfect! My boy got the scrambled eggs and corn beef hash. He said if Dempseys was near where we lived it would be in the weekly rotation for lunch. read more

My wife and i were looking for a nice bfast place with a chill atmosphere. We decide to see how this place was. I personally felt like i entered a Retirement home. Old folks everywhere. Everybody was staring. No problem though, we were there for the food. We sat ourselfs, said good morning to the waiter (a blonde chic), she did not respond. She just placed our menus infront and walk away. No smile, no words. 10 mins later, she asked: what we wanted to drink. 2 coffees. She served and walked away. No words. 15 mins later: what would you like. We ordered, then she walk away. No words. We waited a little over 30mins for our food. A guy that arrived way after us got his soup, sandwish and chips before us. When we finally got our food it was semi cold, the waiter sat our plates down and walked away. No words. As we ate, a nice lady in a Red Xmas sweater (maybe the owners wife) came to us and offered coffee refills. Nices person there. Never ones the waiter came to ask if we needed anything else. Ones we finished our meal, the waiter just came to get the plates and left. No words. No how was everything. We got up and went to pay. The only words the waiter said was our bill amount. Overall the food was good. Thank you to lady in the red sweater. The waiter needs to be more on point with the customers needs, try to Smile and be friendly. Our money is green. She might as well held a sign up saying: Whites Only. Sorry to say it, but thats how she made us feel. The 2 star rating represent, the $2 tip we were nice enough to give her. read more

Good food, great service, reasonable prices! Homemade crab soup super tasty. We had 7 people who got a variety of food and it was all good!

Five stars for the waitresses alone! We came in last night after picking up our order from Middletown Sports (thanks Harold!). After settling down at the bar we were greeted with some of the friendliest young ladies! We appreciated their recommendations on the menu. Our soup and sandwiches were yummy. The homemade desserts were great! My daughter loved the chocolate cake with fluffy caramel frosting! We got a great dinner for a good price. We really enjoyed our experience and will be back! read more

What a great place! My Wife said it perfectly, "this takes me back to my childhood!" We had the awesome corned beef hash & eggs and decided to split a couple of pancakes. That was a ton of good food. Finally a great place for good breakfast that isn't far, far away. read more

Nice atmosphere, I visited for breakfast, the sausage gravy was fresh and well prepared, crispy bacon and perfect over easy eggs. I look forward to trying out the lunch menu next time. I will be back soon! :) read more

Crab cake sandwich was delicious!! First time eating here!! I'm definitely coming back, very soon

Oh, I love Dempsey's. Classic "Main Street America" diner, with yummy food that always tastes homemade. Delicious iced tea. When I was pregnant I used to walk there just to get an iced tea (to-go), then walk home. I love it. "Let's go to Dempsey's for Breakfast" is music to my ears. If you go in a couple of times, the staff will start to remember you, they might even have an iced tea sitting at your table before you sit down :-) Great small-town service. Unassuming, unpretentious, and you can watch Main street roll by the windows while you eat. read more

This nice downtown option has wonderful breakfast, lunch and dinner. The inside is a nice and comfy pub-style restaurant that can seat up to 6 people at one table. Their apps and desserts are wonderfully delicious. I would recommend their Jalapeño poppers if you like spicy foods. read more

I went here for lunch today to try it out. Man, I was not disappointed. It's nestled in Middletown, and the town has that small town feel to it. That might explain why the service was so good. I found a table (self seating) and was promptly asked for my order. I ordered the steak and cheese with fries and an iced tea. The waitress brought me my tea while the order cooked, and left a half pitcher of tea on the table for me to use. I really liked that idea, as I didn't have to keep bugging her for more tea. When the food got to me, it was piping hot and huge portions. The steak and cheese had just about everything on it...tomatoes, mayo, lettuce, hots, mushrooms, grilled onions. I could've also gotten jalapenos if I wanted. The fries were done well and crispy. The sandwich was one of the best tasting steak and cheeses I've ever had, and I've tried great ones in both Jersey and Philly. The only complaint I'd have is I felt it was a little pricey. The steak and cheese (foot long), fries and iced tea was just shy of $20. Not outrageous, but a little more than I'd like to pay. I'm going to try their breakfast sometime soon, as I've heard that is also great. Overall, great experience. One more thing. They're apparently open during the week until 8pm, only 2pm on Saturday and Sunday, and closed Monday. Not sure I get that, but that's ok. I'll go during the week. read more

Dempseys Grille - This steak and cheese was loaded, and very tasty! - Diners Near Me - Middletown, Maryland

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First time here this morning! Fabulous breakfast. Very good Diner food. Great little place. Clean and welcoming.

As diners go, this is a good un! Can't beat CHEAP slightly greasy food on a historic main street. The desserts are a must.

Small hometown feel, the staff is wonderful and the food is great! We often dine there for breakfast. You can't go wrong with any of the "go to" items such as waffles, pancakes or eggs. The home fries are to DIE FOR!! Listen, I'm not a potato fan, but you have to try the home fries. Can't go wrong with the grits. If you like iced tea, you'll love their freshly brewed sweet or unsweet. Kid friendly, family friendly, people friendly. Enjoy! read more

Good down home cooking. Friendly service. Very clean. Will definitely be back! Very affordable too!

Not sure if we just hit a bad time, but it was after breakfast rush, so less than 1/3 full. Ordered, then after 35 min noticed nothing going on in small kitchen. Finally after 45 min we asked if breakfast was started. "No, guess not", was reply by waitress. Table next to us was in the same boat. A joke to call this a service business. read more

We eat here quite often. The food is always good. You may have to wait depending on the time of day but we have never had a bad meal. Great servers. read more

(10/30/2013) Good, basic, little diner on a quaint main street in a rural town. Open early for breakfast, serves the standards. Wandered in around 10:30 am on a weekday, grills already switched over from breakfast to lunch. Started with a cup of the Chicken and Corn Soup (like classic chicken noodle with lots of dried parsley and canned corn); chicken-y well-salted, but not salty, some coagulated proteins in the broth, chock full of lots of shredded chicken breast and curly wide egg noodles. Had a Grilled Reuben, piled thick with salty decent quality corned beef, 2 slices of Swiss and plenty of Thousand Island dressing. Sandwich was griddled pale golden and came very quickly, maybe too quickly, some parts of the sandwich were stone cold, parts of the cheese were not melted. Overall, good value, mostly friendly (some paranoid vibes when I took a few snaps, maybe that's unusual out here, or maybe I just don't look like I'm from around these parts). read more

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This place was what I was looking for. A small town diner with great tasting food and good prices. The staff was friendly and the service was quick for what I expected. We will be back for sure read more

This is a very family-friendly restaurant and all of the servers are extremely welcoming. Great place to go for some comfort food!

Stopped by yesterday before going on the second stop of our Ice Cream road trip. Used the reviews (both here and other reviewers) to pick Dempsey's. Very pleased. The food was well worth the trip. Penny (the waitress) made the stop even better. All four in my group agreed. Some place well worth going back to. read more